Britney Spears' Fiancé Sam Asghari Is 'Encouraging Her' as She Figures Out Her Next Steps: Source

The next couple of months will certainly be a transition for Britney Spears, but she has her fiancé Sam Asghari by her side.

Nearly a week after an L.A. County judge terminated her conservatorship, a source tells PEOPLE that the pop star hopes to "stay healthy" and she's being encouraged by her beau to keep going.

"Britney basically went from not being able to do what she wants, to being able to do anything she wants. The big question now is, 'What is she going to do?' " the source tells PEOPLE. "Sam is encouraging her to stay on a schedule. He is very focused and likes to feel accomplished."

The insider adds, "Britney and Sam are having fun together. She loves having him around."

Spears, 39, and Asghari, 27, celebrated the end of her conservatorship by wearing "free Britney" T-shirts last Friday.

"History was made today. Britney is Free!" he captioned the post. (Spears and Asghari got engaged in September.)

As part of her adjustment, the singer will be supported by a "termination plan" aimed at helping her with her "ongoing needs and best interests." The source says Spears helped develop said plan.

"She has a great plan in place that she developed with Jodi [Montgomery]," the source says. "Britney wants to stay healthy."

Before the end of her conservatorship, her former personal conservator Montgomery filed a sealed termination plan — which details some of the singer's "sensitive and private" health information — that would aid her in "supportive decision-making."

The plan is one Montgomery has been working on since late June, when Spears addressed the court and requested the end of her conservatorship, calling it "abusive." In a statement to PEOPLE at the time, Wright said Montgomery looked "forward" to presenting the care plan and "supporting Britney through the process."

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And following Friday's hearing where Spears' conservatorship was ended, a rep for Montgomery shared to PEOPLE that Montgomery was "happy" to continue helping Spears in her adjustment over the coming months.

"Throughout the conservatorship, Ms. Montgomery has been a tireless advocate for Ms. Spears and it has always been her goal to give Ms. Spears a path towards the termination of her conservatorship," Montgomery's rep from EMC Bowery told PEOPLE. "That day is now here."

The statement continued, "Ms. Montgomery is happy to continue working for Ms. Spears and assisting Ms. Spears in her freedom, independence, growth, wellness, and happiness outside of the conservatorship."